Alkylidene Bisamides Research Articles

Fabrication of a novel graphene oxide based magnetic nanocomposite and its usage as a highly effectual catalyst for the construction of N,N'-alkylidene bisamides.

At first, a novel graphene oxide-based magnetic nanocomposite namely Si-propyl-functionalized N 1,N 1,N 2,N 2-tetramethylethylenediamine-N 1,N 2-diium hydrogen sulfate anchored to graphene oxide-supported Fe3O4 (nano-[GO@Fe3O4@R-NHMe2][HSO4]) was fabricated. After full characterization of the nanocomposite, its catalytic performance was examined for the solvent-free construction of N,N'-alkylidene bisamides from aryl aldehydes (1 eq.) and primary aromatic and aliphatic amides (2 eq.), in which the products were acquired in short times (15-30 min) and high to excellent yields (89-98%). Nano-[GO@Fe3O4@R-NHMe2][HSO4] could be magnetically isolated form the reaction medium, and reused three times without remarkable loss of catalytic activity.

Synthesis of N,N′-alkylidene bisamides and Suzuki–Miyaura coupling reaction derivatives with Pd organometallic catalyst anchored to channels of mesoporous silica MCM-41

At first, an organometallic catalyst namely, Pd-DPyE@MCM-41@MNP was prepared through magnetic (Fe3O4) nanoparticles-doped into channels of mesoporous silica MCM-41 and then, anchoring a novel complex composed of di(4-pyridyl)ethylene and palladium on the inner surface of the support. This immobilized catalyst was successfully identified via VSM, ICP-OES, TEM, FTIR, TGA, SEM, BET, XRD, EDX and elemental mapping analyses. After that, it was used as a versatile, heterogeneous, and magnetically reproducible catalyst in the generation of N,N′-alkylidene bisamides (1a-13a, 8–20 min, 90–98%, 50 °C, solvent-free) and Suzuki–Miyaura coupling (SMC) reaction derivatives (1b-26b, 10–140 min, 86–98%, 60 °C, PEG-400). The VSM plot of Pd-DPyE@MCM-41@MNP displays that this nanocatalyst can be easily recycled by applying an external magnetic field. In both synthetic paths, this nanocatalyst was reused at least seven times without palladium leaching and significantly reducing its catalytic performance. Also, stability and heterogeneous nature of catalyst were approved via ICP-OES technique and hot filtration test.

Solar-Assisted Green Synthesis, Molecular Docking, Antibacterial, and Cytotoxicity Studies of Symmetrical N, N’-Alkylidene Bisamides Bearing Lower E-Factors

N, N'-alkylidene bisamides show promise in biological and pharmaceutical uses. Advanced chemistry now explores cleaner and more environmentally friendly methods. One such method involves using concentrated solar radiation (CSR) to facilitate the green synthesis of N, N'-alkylidene bisamides. This approach simplifies the process by combining aldehydes and amides in a one-pot reaction. Its solvent-free nature sets it apart, aligning with environmentally friendly practices. Any regular catalyst aids the response, making it efficient. The simplicity continues with an easy filtration step to isolate the products. Notably, there's no need for column chromatography, making the purification process straightforward. In general, a mixture of aldehyde, aryl/alkylamide was taken in a round bottom flask. The reaction mass in RBF was then kept under the concentrated solar radiation (CSR) setup with continuous stirring on a magnetic stirrer. After few hours of stirring the precipitate was observed. After completion of the reaction, the precipitated product was washed with water and recrystallized from hot ethanol to afford pure product symmetrical N, N'-alkylidene bisamide. Dimethyl sulfoxide (DMSO) was used as a solvent to prepare a stock of derivatives. Luria Bertani broth (LB) used for the present study viz; Staphylococ-cus aureus MCC 2408, Escherichia coli MCC 2412, Pseudomonas aeruginosa MCC 2080 and Klebsiella pneumoniae MCC 2451 used to evaluate the antibacterial property of the derivatives. Indeed, this method offers an eco-friendly solution and showcases the potential of using renewable energy sources in chemical synthesis. It is a significant step towards sustainable practices in chemistry, particularly in producing complex organic compounds for biological and pharmaceutical purposes.

Nano-[Mn-PSMP]Cl2 as a new Schiff base complex and catalyst for the synthesis of N,N'-alkylidene bisamides

Nano-[Mn-PSMP]Cl2 as a new Schiff base complex and catalyst for the synthesis of N,N'-alkylidene bisamides

Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N,N′‐alkylidene bisamides

In this research, a novel organic–inorganic hybrid salt, namely, N1,N1,N2,N2‐tetramethyl‐N1,N2‐bis(sulfo)ethane‐1,2‐diaminium tetrachloroferrate ([TMBSED][FeCl4]2) was prepared and characterized by Fourier‐transform infrared spectroscopy (FT‐IR), energy‐dispersive X‐ray spectroscopy (EDX), elemental mapping, field emission scanning electron microscopy (FE‐SEM), X‐ray diffraction (XRD), thermal gravimetric (TG), differential thermal gravimetric (DTG), and vibrating‐sample magnetometry (VSM) analyses. Catalytic activity of the hybrid salt was tested for the synthesis of N,N′‐alkylidene bisamides through the reaction of benzamide (2 eq.) and aromatic aldehydes (1 eq.) under solvent‐free conditions in which the products were obtained in high yields and short reaction times. The catalyst was superior to many of the reported catalysts in terms of two or more of these factors: the reaction medium and temperature, yield, time, and turnover frequency (TOF). [TMBSED][FeCl4]2 is a Brønsted–Lewis acidic catalyst; there are two SO3H groups (as Brønsted acidic sites) and two tetrachloroferrate anions (as Lewis acidic sites) in its structure. Highly effectiveness of the catalyst for the synthesis of N,N′‐alkylidene bisamides can be attributed to synergy of the Brønsted and Lewis acids and also possessing two sites of each acid.

Graphene oxide anchored with sulfonic acid-functionalized glycerin: production, characterization and catalytic performance for the synthesis of N,N′-alkylidene bisamides

A novel nanosheet-structured material, namely graphene oxide anchored with sulfonic acid-functionalized glycerin (GO@Gl-SO3H), was prepared and characterized by FTIR, EDS, FESEM, TEM and XRD analyses. Afterward, its catalytic performance was examined for the synthesis of N,N′-alkylidene bisamides through the reaction of benzamide (2 eq.) and arylaldehydes (1 eq.) under solvent-free conditions. GO@Gl-SO3H was a highly effective catalyst for the reaction and afforded the products in high yields and short reaction times.

N,N,N′,N′-Tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate and pyridinium-N-sulfonic acid hydrogen sulfate as highly effective dual-functional catalysts for the preparation of N,N′-alkylidene bisamides

Abstract In this research, Brønsted-acidic ionic liquids N,N,N′,N′-tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate ([TMEDSA][TFA]2) and pyridinium-N-sulfonic acid hydrogen sulfate ([Py-SO3H][HSO4]) have been introduced as dual-functional catalysts for the green, simple and effective preparation of N,N′-alkylidene bisamides by the reaction of primary amides (2 eq.) with arylaldehydes (1 eq.) under solvent-free conditions. The reaction results and conditions of the catalysts have been compared with the previously reported ones. [TMEDSA][TFA]2 and [Py-SO3H][HSO4] were superior to the previously reported catalysts in terms of two or more of these factors: reaction times (10–45 min), yields (86–98%), temperature and the reaction conditions. Additionally, a plausible and attractive mechanism based on dual functionality of the catalysts has been proposed.

A Nanostructured Organic‐Inorganic Hybrid Material: Preparation, Characterization and Catalytic Performance for the Synthesis of N,N′‐Alkylidene Bisamides

AbstractIn this research, a novel nanostructured mesoporous organic‐inorganic hybrid material, based on dicationic ionic liquid‐anchored with silica, namely nano‐2‐[N′,N′‐dimethyl‐N′‐(silica‐n‐propyl)ethanaminium chloride]‐N,N‐dimethylaminium bisulfate {nano‐[DSPECDA][HSO4]} has been prepared, and characterized by FT‐IR, energy‐dispersive X‐ray spectroscopy (EDX), field emission scanning electron microscopy (FE‐SEM), X‐ray diffraction (XRD), thermal gravimetry (TG), differential thermal gravimetric (DTG), differential thermal analysis (DTA), and adsorption/desorption porosimetry (BET, Langmuir, adsorption/desorption isotherm, BJH, and t‐plot) methods. Thereafter, the nanomaterial has been utilized as a highly effectual, heterogeneous and recyclable nanocatalyst for the synthesis of N,N′‐alkylidene bisamides via the condensation reaction of arylaldehydes (1 eq.) with primary amides (2 eq.) under solvent‐free conditions. The reaction results were better compared with the literature in terms of two or more of these factors: turnover frequency (TOF), yield, temperature, time, and the reaction media. Moreover, a plausible mechanism for the synthesis has been proposed.

Synthesis, characterization and application of nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride as a highly efficient catalyst for the preparation of N,N′-alkylidene bisamides

A novel mesoporous nanomaterial, namely nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-[TSPSED][Cl]2), was prepared, and characterized using Fourier-transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDS), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), adsorption/desorption porosimetry (BET, Langmuir, BJH and adsorption/desorption isotherm), thermal gravimetric (TG), differential thermal gravimetric (DTG) and X-ray diffraction (XRD) analyses. Afterward, nano-[TSPSED][Cl]2 was used as a highly efficient and recyclable nanocatalyst for the condensation reaction of primary amides (2 eq.) with arylaldehydes (1 eq.) under solvent-free conditions to afford N,N′-alkylidene bisamides in high yields and in short times.

Immobilization of dihydrogen phosphate onto rice husk ash as a highly efficient and green catalyst for the synthesis of symmetrical N,N′-alkylidene bisamides

The preparation and characterization of an environmentally-benign and low-cost catalyst consisting of KH2PO4 supported on silica from rice husk ash is reported. The prepared catalyst was characterized by FT-IR spectroscopy, field emission scanning electron microscopy, powder X-ray diffraction and inductively coupled plasma. The synthesized nanocomposite exhibited an excellent catalytic efficiency in the condensation reaction for the preparation of symmetrical N,N′-alkylidene bisamides under solvent-free conditions.

A green procedure for one-pot synthesis of N, N’-alkylidene bisamides under solvent- and catalyst-free conditions

An effective solvent- and catalyst-free method was introduced for synthesis of symmetrical N, N’-alkylidene bisamides as high usage compounds in organic chemistry. In order to show the generality, the synthesis was done with various benzamides and aldehydes to obtain various derivatives in high yields.

Synthesis and Characterization of a New Nano Ionic Liquid Based on Dawson-Type Polyoxometalate and Its Application in the Synthesis of Symmetrical N,N′-Alkylidene Bisamides

A new organic-inorganic nano hybrid ionic liquid based on polyoxometalate H2 [MIMBS]4 [P2W18O62]·11 H2O (MIMBS − P2W18), originated from self-assembling of Dawson-type polyoxometalate [P2W18 O62]6− and organic ionic liquid [1-(3-sulfonic group) butyl-3-methyl imidazolium (MIMBS)] components, has been successfully prepared and characterized by elemental analysis, Fourier transform infrared (FT-IR), 1H, 13C, and 15P nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), powder X-ray diffraction (XRD), scanning electron microscopy (SEM) and energy dispersive X-ray analysis (EDX). The analysis results present that the size range of the nanosheets are between 40 and 50 nm. The resulting heterogeneous catalyst is shown to be an efficient acidic catalyst for the synthesis of symmetrical N, N′-alkylidene bisamides under solvent-free conditions at 80 °C in high yields. After completion of reaction, the catalyst was simply recovered by filtration and recycled without significant loss in the catalytic activity. The hallmark privileges presented by this method are green chemistry, mild condition, simple method and great yield.

Synthesis and characterization of ZnO incorporated magnetically recoverable KIT-6 as a novel and efficient catalyst in the preparation of symmetrical N, N′-alkylidene bisamides

A novel magnetically recoverable nanocomposite consisting of the NiFe2O4 core and KIT-6 mesoporous silica shell incorporated with ZnO nanoparticles was constructed. This nanocomposite was characterized by Fourier transform infrared (FT-IR), powder X-ray diffraction (XRD), Brunauer Emmett Teller (BET), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM) and vibrating sample magnetometry (VSM). This new nanocomposite demonstrated a catalytic performance in the synthesis of symmetrical N,N′-alkylidene bisamides at the condensation reaction under solvent-free conditions. The nanocatalyst could simply be recovered from the reaction environment by using an exterior magnet and reused five times without a remarkable losing in the catalytic property.

One-pot multi-component synthesis of N,N′-alkylidene bisamides and imidazoles using heteropoly-11-tungsto-1-vanadophosphoric acid supported on natural clay as catalyst: A green approach

ABSTRACTOne-pot multi-component synthesis of N,N′-alkylidene bisamides, 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in the presence of catalytic material heteropoly-11-tungsto-1-vanadophosphoric acid (HPV) supported on activated natural clay for about 20% (HPVAC-20) under solvent-free reaction condition have been achieved. Green heterogeneous reaction condition, simple workup procedure, short reaction time, high yield of products, and reusability of the catalyst are the advantages of this protocol.

An efficient synthesis of bis(indolyl) methanes and N,N′-alkylidene bisamides by Silzic under solvent free conditions

An operationally simple and green method for the synthesis of a wide range of bis(indolyl)methanes, and N,N′-alkylidene bisamides under mild conditions, with excellent yields using Silzic, has been developed. This improved method furnishes in good yields bis(indolyl)methanes derivatives starting from indole and aldehydes, or ketones, and N,N′-alkylidene bisamides derivatives starting from acetamide and aldehydes. The catalytic system was reused up to three times with the same efficiency.

An Efficient Synthesis of Symmetrical N,N′-Alkylidene bis-Amides Catalyzed by a Heteropolyacid

Amides and polyamides have been found as a key component of many biologically active and pharmaceutically useful compounds. In particular, symmetrical and unsymmetrical N,N′-alkylidene bis-amides a...

Synthesis of symmetrical N,N′-alkylidene bis-amides catalyzed by silica coated magnetic NiFe2O4 nanoparticle supported polyphosphoric acid (NiFe2O4@SiO2-PPA) and its application toward silver nanoparticle synthesis for electrochemical detection of glucose

For the first time, a new and facile Ag@PM-b-B nanocomposite electrochemical sensor was successfully developed for the detection of glucose. Also, the magnetically recoverable catalyst was easily recycled at least ten times without significant loss of catalytic activity.

Efficient Synthesis of Symmetrical N,N‘-Alkylidene Bisamides Catalysed by Acetyl Chloride

Symmetrical bisamides were synthesised from aldehydes and amides in the presence of distilled acetyl chloride. The reaction is rapid, clean and gives the products in excellent yields.

ChemInform Abstract: Efficient Synthesis of Symmetrical Bisamides from Aldehydes and Amides Catalyzed by Silica‐Bonded S‐Sulfonic Acid Nanoparticles.

Abstract Silica-bonded S-sulfonic acid nanoparticles (SBSSANPs) were easily synthesized from silica nanoparticles and showed to be an efficient catalyst in the synthesis the symmetrical N,N′-alkylidene bisamides. Reaction of aldehydes and amides in the presence of the catalyst afforded the corresponding bisamides in good to excellent yields. The extensive range of substrates suggests general applicability of the method. Reusability of the catalyst, simple workup procedure, and short reaction times are other advantages of this protocol. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications ® to view the free supplemental file.

Efficient Synthesis of Symmetrical Bisamides from Aldehydes and Amides Catalyzed by Silica-Bonded S-Sulfonic Acid Nanoparticles

Silica-bonded S-sulfonic acid nanoparticles (SBSSANPs) were easily synthesized from silica nanoparticles and showed to be an efficient catalyst in the synthesis the symmetrical N,N′-alkylidene bisamides. Reaction of aldehydes and amides in the presence of the catalyst afforded the corresponding bisamides in good to excellent yields. The extensive range of substrates suggests general applicability of the method. Reusability of the catalyst, simple workup procedure, and short reaction times are other advantages of this protocol. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications ® to view the free supplemental file.